Aaron Carter
Then: Following in the footsteps of older brother Nick Carter of the Backstreet Boys, little bro Aaron went on to pursue his own pop career. In ’97 he released his first single, “Crush on You.” 2000 brought us “Aaron’s Party (Come Get It)” and “I Want Candy.” Carter opened at several Britney Spears’ concerts. He dated both Lizzie McGuire and LiLo (Hilary Duff and Lindsay Lohan), reportedly causing a feud between the two stars.
Now: Now: In 2013 when Carter began touring again, he filed for bankruptcy, claiming he owed over 3.5 million in debt from the height of his fame. As of 2014, he reportedly settled his debt. He’s still touring today, and is planning on releasing new music this year. Oh, and apparently he still loves Hil Duff.
[Photo via @aaroncarter and @aaroncarter]